Molecular sieve ssz-120, its synthesis and use

ABSTRACT

A small crystal size, high surface area aluminogermanosilicate molecular sieve material, designated SSZ-120, is provided. SSZ-120 can be synthesized using 3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium] dications as a structure directing agent. SSZ-120 may be used in organic compound conversion reactions and/or sorptive processes.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a divisional application of U.S. patent applicationSer. No. 17/323,005 filed on May 18, 2021, which claims priority to andthe benefit of U.S. Provisional Application Ser. No. 63/028,642 filed onMay 22, 2020.

FIELD

This disclosure relates to a small crystal size, high surface areaaluminogermanosilicate molecular sieve designated SSZ-120, itssynthesis, and its use in organic compound conversion reactions andsorption processes.

BACKGROUND

Molecular sieves are a commercially important class of materials thathave distinct crystal structures with defined pore structures that areshown by distinct X-ray diffraction (XRD) patterns and have specificchemical compositions. The crystal structure defines cavities and poresthat are characteristic of the specific type of molecular sieve.

According to the present disclosure, a small crystal size, high surfacearea aluminogermanosilicate molecular sieve, designated SSZ-120 andhaving a unique powder X-ray diffraction pattern, has been synthesizedusing3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications as a structure directing agent.

SUMMARY

In a first aspect, there is provided an aluminogermanosilicate molecularsieve having, in its calcined form, a powder X-ray diffraction patternincluding the peaks in the following table:

2-Theta d-Spacing Relative Intensity [°] [nm] [100 × I/Io] 6.8 1.30 W9.5 0.93 W 15.6 0.57 M 21.0 0.42 W 22.2 0.40 VS 25.9 0.34 M 26.9 0.33 M

The calcined molecular sieve can have a total surface area (asdetermined by the t-plot method for nitrogen physisorption) of at least500 m²/g and/or an external surface area (as determined by the t-plotmethod for nitrogen physisorption) of at least 100 m²/g.

In a second aspect, there is provided an aluminogermanosilicatemolecular sieve having, in its as-synthesized form, a powder X-raydiffraction pattern including the peaks in the following table:

2-Theta d-Spacing Relative Intensity [°] [nm] [100 × I/Io] 6.8 1.31 W9.4 0.94 W 15.7 0.57 M 21.0 0.42 M 22.0 0.40 VS 25.9 0.34 M 26.9 0.33 M

In its as-synthesized and anhydrous form, the aluminogermanosilicatemolecular sieve can have a chemical composition comprising the followingmolar relationship:

Broadest Secondary (SiO₂ + GeO₂)/Al₂O₃ ≥30 ≥60 Q/(SiO₂ + GeO₂) >0 to0.1 >0 to 0.1wherein Q comprises3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications.

In a third aspect, there is provided a method of synthesizing analuminogermanosilicate molecular sieve, the method comprising (1)providing a reaction mixture comprising: (a) a FAU framework typezeolite; (b) a source of germanium; (c) a structure directing agent (Q)comprising3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications; (d) a source of fluoride ions; and (e) water; and (2)subjecting the reaction mixture to crystallization conditions sufficientto form crystals of the aluminogermanosilicate molecular sieve.

In a fourth aspect, there is provided a process of converting afeedstock comprising an organic compound to a conversion product whichcomprises contacting the feedstock at organic compound conversionconditions with a catalyst comprising an active form of thealuminogermanosilicate molecular sieve, described herein.

In a fifth aspect, there is provided an organic nitrogen compoundcomprising a dication having the following structure:

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the powder X-ray diffraction (XRD) pattern of theas-synthesized product of Example 2.

FIGS. 2(A)-2(D) show scanning electron micrograph (SEM) images of theas-synthesized product of Example 2 at different magnifications.

FIG. 3 shows the powder XRD pattern of the calcined product of Example3.

FIG. 4 is a graph illustrating the relationship between conversion oryield and temperature in the hydroconversion of n-decane over aPd/SSZ-120 catalyst.

DETAILED DESCRIPTION Definitions

The term “framework type” has the meaning described in the “Atlas ofZeolite Framework Types”, by Ch. Baerlocher and L. B. McCusker and D. H.Olsen (Sixth Revised Edition, Elsevier, 2007).

The term “zeolite” refers an aluminosilicate molecular sieve having aframework constructed of alumina and silica (i.e., repeating AlO4 andSiO4 tetrahedral units).

The term “aluminogermanosilicate” refers to a molecular sieve having aframework constructed of AlO4, GeO4 and SiO4 tetrahedral units. Thealumingermanosilicate may contain only the named oxides, in which case,it may be described as a “pure aluminogermanosilicate” or it may containother additional oxides as well.

The term “as-synthesized” is employed herein to refer to a molecularsieve in its form after crystallization, prior to removal of thestructure directing agent.

The term “anhydrous” is employed herein to refer to a molecular sievesubstantially devoid of both physically adsorbed and chemically adsorbedwater.

The term “SiO₂/Al₂O₃ molar ratio” may be abbreviated as “SAR”.

Synthesis of the Molecular Sieve

Aluminogermanosilicate molecular sieve SSZ-120 can be synthesized by:(1) providing a reaction mixture comprising (a) a FAU framework typezeolite; (b) a source of germanium; (c) a structure directing agent (Q)comprising3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications; (d) a source of fluoride ions; and (e) water; and (2)subjecting the reaction mixture to crystallization conditions sufficientto form crystals of the aluminogermanosilicate molecular sieve.

The reaction mixture can have a composition, in terms of molar ratios,within the ranges set forth in Table 1:

TABLE 1 Reactants Broadest Secondary (SiO₂ + GeO₂)/Al₂O₃  30 to 600  60to 500 Q/(SiO₂ + GeO₂) 0.10 to 1.00 0.20 to 0.70 F/(SiO₂ + GeO₂) 0.10 to1.00 0.20 to 0.70 H₂O/(SiO₂ + GeO₂)  2 to 10 4 to 8wherein Q comprises3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications.

In some aspects, the reaction mixture can have a SiO₂/GeO₂ molar ratioin a range of from 4 to 12 (e.g., from 6 to 10).

The FAU framework type zeolite can be ammonium-form zeolites orhydrogen-form zeolites (e.g., NH₄-form zeolite Y, H-form zeolite Y).Examples of the FAU framework type zeolite include zeolite Y (e.g.,CBV720, CBV760, CBV780, HSZ-385HUA, and HSZ-390HUA). Preferably, the FAUframework type zeolite is zeolite Y. More preferably, zeolite Y has aSiO₂/Al₂O₃ molar ratio in a range of about 30 to about 500. The FAUframework type zeolite can comprise two or more zeolites. Typically, thetwo or more zeolites are Y zeolites having different SiO2/Al₂O₃ molarratios. The FAU framework type zeolite can also be the only silica andaluminum source to form the aluminogermanosilicate molecular sieve.

Sources of germanium include germanium oxide and germanium alkoxides(e.g., germanium ethoxide).

Sources of fluoride ions include hydrogen fluoride, ammonium fluoride,and ammonium bifluoride.

SSZ-120 can be synthesized using a structure directing agent (Q)comprising3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications, represented by the following structure (1):

Suitable sources of Q are the hydroxides, chlorides, bromides, and/orother salts of the diquaternary ammonium compound.

The reaction mixture can contain seeds of a molecular sieve material,such as SSZ-120 from a previous synthesis, in an amount of from 0.01 to10,000 ppm by weight (e.g., 100 to 5000 ppm by weight) of the reactionmixture. Seeding can be advantageous to improve selectivity for SSZ-120and/or to shorten the crystallization process.

It is noted that the reaction mixture components can be supplied by morethan one source. Also, two or more reaction components can be providedby one source. The reaction mixture can be prepared either batchwise orcontinuously.

Crystallization and Post-Synthesis Treatment

Crystallization of the molecular sieve from the above reaction mixturecan be carried out under either static, tumbled or stirred conditions ina suitable reactor vessel, such as polypropylene jars or Teflon-lined orstainless-steel autoclaves placed in convection oven maintained at atemperature of from 100° C. to 200° C. for a time sufficient forcrystallization to occur at the temperature used (e.g., 1 day to 14days). The hydrothermal crystallization process is usually conductedunder autogenous pressure.

Once the desired molecular sieve crystals have formed, the solid productis separated from the reaction mixture by standard separation techniquessuch as filtration or centrifugation. The recovered crystals arewater-washed and then dried, for several seconds to a few minutes (e.g.,from 5 seconds to 10 minutes for flash drying) or several hours (e.g.,from 4 to 24 hours for oven drying at 75° C. to 150° C.), to obtainas-synthesized SSZ-120 crystals having at least a portion of thestructure directing agent within its pores. The drying step can beperformed at atmospheric pressure or under vacuum.

The as-synthesized molecular sieve may be subjected to thermaltreatment, ozone treatment, or other treatment to remove part or all ofthe structure directing agent used in its synthesis. Removal of thestructure directing agent may be carried out by thermal treatment (i.e.,calcination) in which the as-synthesized molecular sieve is heated inair or inert gas at a temperature sufficient to remove part or all ofthe structure directing agent. While sub-atmospheric pressure may beused for the thermal treatment, atmospheric pressure is desired forreasons of convenience. The thermal treatment may be performed at atemperature at least 370° C. for at least a minute and generally notlonger than 20 hours (e.g., from 1 to 12 hours). The thermal treatmentcan be performed at a temperature of up to 925° C. For example, thethermal treatment may be conducted at a temperature of from 400° C. to600° C. in air for approximately 1 to 8 hours. The thermally-treatedproduct, especially in its metal, hydrogen and ammonium forms, isparticularly useful in the catalysis of certain organic (e.g.,hydrocarbon) conversion reactions.

Any extra-framework metal cations in the molecular sieve can be replacedin accordance with techniques well known in the art (e.g., by ionexchange) with hydrogen, ammonium, or any desired metal cation.

Characterization of the Molecular Sieve

In its as-synthesized and anhydrous form, molecular sieve SSZ-120 canhave a chemical composition comprising the following molar relationshipset forth in Table 2:

TABLE 2 Broadest Secondary (SiO₂ + GeO₂)/Al₂O₃ ≥30 ≥60 Q/(SiO₂ +GeO₂) >0 to 0.1 >0 to 0.1wherein Q comprises3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dications.

In some aspects, the molecular sieve can have a SiO₂/GeO₂ molar ratio ina range of from 4 to 12 (e.g., 6 to 10).

In its calcined form, molecular sieve SSZ-120 can have a chemicalcomposition comprising the following molar relationship:

Al₂O₃:(n)(SiO₂+GeO₂)

wherein n is ≥30 (e.g., 30 to 600, ≥60, 60 to 500, or 100 to 300).

Molecular sieve SSZ-120 has a powder X-ray diffraction pattern which, inits as-synthesized form, includes at least the peaks set forth in Table3 below and which, in its calcined form, includes at least the peaks setforth in Table 4.

TABLE 3 Characteristic Peaks for As-Synthesized SSZ-120 2-Thetad-Spacing Relative Intensity [°] [nm] [100 × I/Io] 6.8 1.31 W 9.4 0.94 W15.7 0.57 M 21.0 0.42 M 22.0 0.40 VS 25.9 0.34 M 26.9 0.33 M

TABLE 4 Characteristic Peaks for Calcined SSZ-120 2-Theta d-SpacingRelative Intensity [°] [nm] [100 × I/Io] 6.8 1.30 W 9.5 0.93 W 15.6 0.57M 21.0 0.42 W 22.2 0.40 VS 25.9 0.34 M 26.9 0.33 M

The powder X-ray diffraction patterns presented herein were collected bystandard techniques using copper K-alpha radiation. As will beunderstood by those of skill in the art, the determination of theparameter 2-theta is subject to both human and mechanical error, whichin combination can impose an uncertainty of about ±0.3° on each reportedvalue of 2-theta. This uncertainty is, of course, also manifested in thereported values of the d-spacings, which are calculated from the 2-thetavalues using Bragg's law. The relative intensities of the lines, I/Io,represents the ratio of the peak intensity to the intensity of thestrongest line, above background. The intensities are uncorrected forLorentz and polarization effects. The relative intensities are given interms of the symbols VS=very strong (>60 to 100), S=strong (>40 to 60),M=medium (>20 to 40), and W=weak (>0 to 20).

Minor variations in the powder X-ray diffraction pattern (e.g.,experimental variation in peak ratios and peak positions) can resultfrom variations in the atomic ratios of the framework atoms due tochanges in lattice constants. In addition, sufficiently small crystalsmay affect the shape and intensity of peaks, possibly leading to peakbroadening. Calcination can also cause minor shifts in the powder X-raydiffraction pattern compared to the pre-calcination powder X-raydiffraction pattern. Notwithstanding these minor perturbations, thecrystal lattice structure may remain unchanged following calcination.

The syntheses described herein can produce a molecular sieve having asmall crystal size, such that the total surface area of the material canbe at least 500 m²/g and the external surface area can be at least 100m²/g. In some aspects, the molecular sieve described herein can comprisecrystals having a total external surface area of at least 600 m²/g, atleast 625 m²/g, at least or at least 650 m²/g, such as from 500 to 800m²/g, from 600 to 800 m²/g, or from 650 to 800 m²/g. Additionally oralternatively, the molecular sieve described herein can comprisecrystals having an external surface area of at least 100 m²/g, at least110 m²/g, at least 120 m²/g, at least 130 m²/g, or at least 140 m²/g,such as from 100 to 300 m²/g, from 120 to 300 m²/g, or from 140 to 300m²/g. All surface area values given herein are determined from nitrogenphysisorption using the t-plot method. Details of this method aredescribed by B. C. Lippens and J. H. de Boer (J. Catal. 1965, 4,319-323).

INDUSTRIAL APPLICABILITY

Molecular sieve SSZ-120 (where part or all of the structure directingagent is removed) may be used as a sorbent or as a catalyst to catalyzea wide variety of organic compound conversion processes including manyof present commercial/industrial importance. Examples of chemicalconversion processes which are effectively catalyzed by SSZ-120, byitself or in combination with one or more other catalytically activesubstances including other crystalline catalysts, include thoserequiring a catalyst with acid activity. Examples of organic conversionprocesses which may be catalyzed by SSZ-120 include aromatization,cracking, hydrocracking, disproportionation, alkylation,oligomerization, and isomerization.

As in the case of many catalysts, it may be desirable to incorporateSSZ-120 with another material resistant to the temperatures and otherconditions employed in organic conversion processes. Such materialsinclude active and inactive materials and synthetic or naturallyoccurring zeolites as well as inorganic materials such as clays, silicaand/or metal oxides such as alumina. The latter may be either naturallyoccurring, or in the form of gelatinous precipitates or gels, includingmixtures of silica and metal oxides. Use of a material in conjunctionwith SSZ-120 (i.e., combined therewith or present during synthesis ofthe new material) which is active, tends to change the conversion and/orselectivity of the catalyst in certain organic conversion processes.Inactive materials suitably serve as diluents to control the amount ofconversion in a given process so that products can be obtained in aneconomic and orderly manner without employing other means forcontrolling the rate of reaction. These materials may be incorporatedinto naturally occurring clays (e.g., bentonite and kaolin) to improvethe crush strength of the catalyst under commercial operatingconditions. These materials (i.e., clays, oxides, etc.) function asbinders for the catalyst. It is desirable to provide a catalyst havinggood crush strength because in commercial use it is desirable to preventthe catalyst from breaking down into powder-like materials. These clayand/or oxide binders have been employed normally only for the purpose ofimproving the crush strength of the catalyst.

Naturally occurring clays which can be composited with SSZ-120 includethe montmorillonite and kaolin family, which families include thesub-bentonites, and the kaolins commonly known as Dixie, McNamee,Georgia and Florida clays or others in which the main mineralconstituent is halloysite, kaolinite, dickite, nacrite, or anauxite.Such clays can be used in the raw state as originally mined or initiallysubjected to calcination, acid treatment or chemical modification.Binders useful for compositing with SSZ-120 also include inorganicoxides, such as silica, zirconia, titania, magnesia, beryllia, alumina,and mixtures thereof.

In addition to the foregoing materials, SSZ-120 can be composited with aporous matrix material such as silica-alumina, silica-magnesia,silica-zirconia, silica-thoria, silica-beryllia, silica-titania as wellas ternary compositions such as silica-alumina-thoria,silica-alumina-zirconia silica-alumina-magnesia andsilica-magnesia-zirconia.

The relative proportions of SSZ-120 and inorganic oxide matrix may varywidely, with the SSZ-120 content ranging from 1 to 90 wt. % (e.g., 2 to80 wt. %) of the composite.

EXAMPLES

The following illustrative examples are intended to be non-limiting.

Example 1 Synthesis of3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dihydroxide

A 250 mL round bottom flask equipped with a magnetic stir bar wascharged with 5 g of 2,6-bis(bromomethyl)naphthalene, 3.83 g of1,2-dimethylimidazole and 100 mL of methanol. A reflux condenser wasthen attached, and the mixture heated at 65° C. for 3 days. Aftercooling, methanol was removed on a rotary evaporator to provide whitesolids. The initially recovered solids from rotary evaporation werefurther purified by recrystallization from cold ethanol. Therecrystallized dibromide salt was pure by ¹H- and ¹³C-NMR spectroscopy.

The dibromide salt was exchanged to the corresponding dihydroxide saltby stirring it with hydroxide exchange resin in deionized waterovernight. The solution was filtered, and the filtrate was analyzed forhydroxide concentration by titration of a small sample with astandardized solution of 0.1 N HCl.

Example 2

Synthesis of SSZ-120

Into a tared 23 mL Parr reactor was added 0.27 g of Tosoh HSZ-390HUAY-zeolite (SAR=500), 0.05 g of GeO₂ and 2.5 mmol of an aqueous3,3′-[2,6-naphthalenebis(methylene)]bis[1,2-dimethyl-1H-imidazolium]dihydroxide solution. The reactor was then placed in a vented hood andwater was allowed to evaporate to bring the H₂O/(SiO₂+GeO₂) molar ratioto 7 (as determined by the total mass of the suspension). Then, 2.5 mmolof HF was added and the reactor was heated to 160° C. with tumbling at43 rpm for about 7 days. The solid products were recovered bycentrifugation, washed with deionized water and dried at 95° C.

Powder XRD of the as-synthesized product gave the pattern indicated inFIG. 1 and showed the product to be a pure form of a new phase, SSZ-120.Significantly decreased crystal size is inferred from the peakbroadening in the powder XRD pattern.

FIGS. 2(A)-2(D) show illustrative SEM images of the as-synthesizedproduct at various magnifications.

The product had a SiO₂/GeO₂ molar ratio of 8, as determined byInductively Coupled Plasma-Atomic Emission Spectroscopy (ICP-AES).

Example 3 Calcination of SSZ-120

The as-synthesized molecular sieve of Example 1 was calcined inside amuffle furnace under a flow of air heated to 550° C. at a rate of 1°C./minute and held at 550° C. for 5 hours, cooled and then analyzed bypowder XRD.

The powder XRD pattern of the calcined material is shown in FIG. 3 andindicates that the material remains stable after calcination to removethe structure directing agent.

Example 4

Example 2 was repeated using Zeolyst CBV780 Y-zeolite (SAR=80) as theFAU source. Powder XRD showed the product to be SSZ-120.

Example 5

Example 2 was repeated using Zeolyst CBV760 Y-zeolite (SAR=60) as theFAU source. Powder XRD showed the product to be SSZ-120.

The product was calcined as described in Example 2. The surface area ofthe sample was then measured using nitrogen physisorption and the datawere analyzed with the t-plot method. The determined total surface areawas 693 m²/g and the external surface area was 144 m²/g. The microporevolume was 0.2666 cm³/g.

Example 6

Example 2 was repeated using Zeolyst CBV720 Y-zeolite (SAR=30) as theFAU source. Powder XRD showed the product to be SSZ-120.

Example 7 Brønsted Acidity

Brønsted acidity of the molecular sieve of Example 5 in its calcinedform was determined by n-propylamine temperature-programmed desorption(TPD) adapted from the published descriptions by T. J. Gricus Kofke etal. (J. Catal. 1988, 114, 34-45); T. J. Gricus Kofke et al. (J. Catal.1989, 115, 265-272); and J. G. Tittensor et al. (J. Catal. 1992, 138,714-720). A sample was pre-treated at 400° C.-500° C. for 1 hour inflowing dry H₂. The dehydrated sample was then cooled down to 120° C. inflowing dry helium and held at 120° C. for 30 minutes in a flowinghelium saturated with n-propylamine for adsorption. Then-propylamine-saturated sample was then heated up to 500° C. at a rateof 10° C./minute in flowing dry helium. The Brønsted acidity wascalculated based on the weight loss vs. temperature by thermogravimetricanalysis (TGA) and effluent NH₃ and propene by mass spectrometry. Thesample had a Brønsted acidity of 250 μmol/g, indicating that aluminumsites are incorporated into the framework of the molecular sieve.

Example 8 Constraint Index Testing

Constraint Index is a test to determine shape-selective catalyticbehavior in molecular sieves. It compares the reaction rates for thecracking of n-hexane (n-C6) and its isomer 3-methylpentane (3-MP) undercompetitive conditions (see V. J. Frillette et al., J. Catal. 1981, 67,218-222).

The hydrogen form of the molecular sieve prepared per Example 5 waspelletized at 4 kpsi, crushed and granulated to 20-40 mesh. A 0.6 gsample of the granulated material was calcined in air at 540° C. for 4hours and cooled in a desiccator to ensure dryness. Then, 0.47 g ofmaterial was packed into a ¼ inch stainless steel tube with alundum onboth sides of the molecular sieve bed. A furnace (Applied Test Systems,Inc.) was used to heat the reactor tube. Nitrogen was introduced intothe reactor tube at 9.4 mL/minute and at atmospheric pressure. Thereactor was heated to about 700° F. (371° C.), and a 50/50 feed ofn-hexane and 3-methylpentane was introduced into the reactor at a rateof 8 μL/minute. The feed was delivered by an ISCO pump. Direct samplinginto a GC began after 15 minutes of feed introduction. Test data resultsafter 15 minutes on stream (700° F.) are presented in Table 5.

TABLE 5 Constraint Index Test n-Hexane Conversion, % 64.83-Methylpentane Conversion, % 93.3 Feed Conversion, % 79.1 ConstraintIndex (excluding 2MP) 0.39 Constraint Index (including 2MP) 0.39

Example 9 Hydroconversion of n-Decane

Material from Example 5 was calcined in air at 595° C. for 5 hours.After calcination, the material was loaded with palladium by mixing forthree days at room temperature 4.5 g of a 0.148 N NH₄OH solution with5.5 g of deionized water and then a (NH₃)₄Pd(NO₃)₂ solution (buffered atpH 9.5) such that 1 g of this solution mixed in with 1 g of molecularsieve provided a 0.5 wt. % Pd loading. The recovered Pd/SSZ-120 materialwas washed with deionized water, dried at 95° C., and then calcined to300° C. for 3 hours. The calcined Pd/SSZ-120 catalyst was thenpelletized, crushed, and sieved to 20-40 mesh.

0.5 g of the Pd/SSZ-120 catalyst was loaded in the center of a 23inch-long×¼ inch outside diameter stainless steel reactor tube withalundum loaded upstream of the catalyst for preheating the feed (a totalpressure of 1200 psig; a down-flow hydrogen rate of 160 mL/minute whenmeasured at 1 atmosphere pressure and 25° C.; and a down-flow liquidfeed rate of 1 mL/hour). All materials were first reduced in flowinghydrogen at about 315° C. for 1 hour. Products were analyzed by on-linecapillary GC once every 60 minutes. Raw data from the GC was collectedby an automated data collection/processing system and hydrocarbonconversions were calculated from the raw data. Conversion is defined asthe amount n-decane reacted to produce other products (includingiso-C10). Yields are expressed as mole percent of products other thann-decane and include iso-C10 isomers as a yield product. The results areshown in FIG. 4 and indicate that the catalyst is quite active and notparticularly selective for isomerization, making considerable crackedproduct from n-decane.

1. An organic nitrogen compound comprising a dication having thefollowing structure:


2. The organic nitrogen compound of claim 1, wherein the dication isassociated with anionic counterion selected from hydroxide, chloride,bromide, or a combination thereof.